The syntheses of (±)-PGEi and (±)-ll-deoxyprostaglandins in the E: and Fi series have been carried out by conjugate addition of bis(triethyl phosphite)copper(I) cyanide vinyllithium to the substituted cyclopentenones la and lb, and subsequent elaboration of vinylamylcarbinol side chain via the intermediate carboxaldehydes 3b and 3d. The intermediate 3d was also converted to (±)-9-oxo-13-czs-prostenoic acid (6c). These transformations are characterized by high yields and ease of operation. The synthesis of prostaglandins has been the subject of considerable synthetic effort during the past several years. In the course of this work a number of elegant syntheses of prostaglandins have been developed, but, in general, these approaches are lengthy and rather complex in nature.2
Die Umsetzung des Bromids (I) mit dem [aus den Komponenten (II) und (III) gebildeten] Enamin (V) liefert das Pyrrol (IVa) (Hantzsche Pyrrolsynthese) ; Cyclisierung des aus (IVa) über das Mesylat (IVb) erhältlichen Iodids (IVc) gibt das Pyrrolopyrrol (VIa), das über die Stufen (VIb), (VIc) in den Ester (VIIa) bzw. dessen Verseifungsprodukt (VIIb) übergeführt wird.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations –citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.